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Meet Al “Chilly” Wynn of CLEVELAND

Today we’d like to introduce you to Al “Chilly” Wynn

Hi Chilly, we’d love for you to start by introducing yourself.
I started trying to make music when I was around the age of 12-13 yrs old. Me and a few of my neighbors would freestyle over instrumentals and make tapes. Then it lead to rapping in cyphers at parties.
I pretty much left music alone around the time I had to get serious about construction. I had bills to pay and things to do. I worked in residential construction a few years before joining the Laborers International Union of North America, Local 860 out of Cleveland. It’s a great career and I learned and earned a lot. In 2020 during Covid I found myself laid off, and started my own company C.R.E.W. Contractors LLC. We did well for ourselves. Yet, once again music took over my life for the second time. So because of my moment of clarity in 2017, “Chilly Wynn” was branded, and so was my record label. I’ve travelled to a few states, networked with some higher-ups in the industry, performed here or there, social media networking….. 7 yrs later, I’m still working on fire content whenever possible.

We all face challenges, but looking back would you describe it as a relatively smooth road?
It’s definitely been a bumpy ride, far from smooth. A Construction worker putting in long hours, or an hip hop artist working til he can’t stay awake, it gets to you some time. Juggling 2 LLCs could easily become a circus act if you’re not careful. I also had to deal with certain individuals who only see me as a walking dollar sign…. Vultures will try and sell a starving artist lies and charge an arm and a leg, then nothing ever comes of it. On the flip side, there are some solid business minded people out there that help, encourage, and guide you through this gauntlet called the entertainment industry. Progress will be made!

Appreciate you sharing that. What else should we know about what you do?
I love both of my businesses! That’s why I combined the two of them and incorporated Construction nomenclature into my music. (CRG) I love concrete and construction, and I love to rap. So the wordplay comes naturally. I’d say I’m just about as lyrical as one can be. I’m after that “Lyricist of the Year” award.
Some of the the things that set me apart from the competition are that I’m just me. My own people, places, and things shaped and molded me into the man I am today. We each have our own experiences, hence everyone has their own story.

What’s next?
My plans are to continue to grow as a person, artist, and business owner.

I’m looking forward to performing in front of the largest crowd possible!! That’d be pretty dope. I’m gearing up to drop a few videos and this mixtape/album. It should be a good one.

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